


Whumptober 2020

by Pineprin137



Category: Supernatural
Genre: Abandonment, Background Case, Bad Parenting, Betrayal, Blood, Brothers, Buried Alive, Canon-Typical Violence, Caretaking, Cold, Coughing, Cults, Dark, Emotional Hurt, Enemies, Enemies to Friends, Fear, Fluff and Hurt/Comfort, Guilt, Gun Violence, Heavy Angst, Hellhounds, Horror, Human Sacrifice, Hunters & Hunting, Hurt Dean Winchester, Hurt No Comfort, Hurt/Comfort, Implied/Referenced Character Death, Implied/Referenced Rape/Non-con, Injury, John is trying, Major Character Injury, Manhandling, Minions, Nightmares, Non-Sexual Bondage, On the Run, Pain, Parent-Child Relationship, Phobias, Protective Dean Winchester, Protective Sam Winchester, Psychological Torture, Regret, Remorse, Ruler of Hell, Ruler of Hell Crowley (Supernatural), Sacrifice, Siblings, Sick Castiel (Supernatural), Sick Character, Sick Dean Winchester, Single Parents, Torture, Werewolves, Whumptober, Worship, You Have Been Warned, Young Sam Winchester, chilling, like demons not little yellow guys who love bananas, reluctant caregiver, very dark
Language: English
Status: In-Progress
Published: 2020-10-03
Updated: 2020-10-11
Packaged: 2021-03-08 03:08:20
Rating: Explicit
Warnings: Graphic Depictions Of Violence, Major Character Death, Rape/Non-Con
Chapters: 11
Words: 3,201
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26798593
Author URL: https://archiveofourown.org/users/Pineprin137/pseuds/Pineprin137
Summary: This is a collection of stories (lengths vary from drabbles to ficlets) I've written for Whumptober 2020 featuring the Winchesters and their friends/enemies/allies/etc.The chapter titles will include the prompt suggestions and the summaries will include the one(s) I chose.
Comments: 7
Kudos: 18





	1. Waking Up Restrained/ Shackled/ Hanging

**Author's Note:**

> WARNING: This is NOT a happy story. This is dark and twisty and all kinds of wrong. A friend asked me about Whumptober and I got the inspiration to participate. But this is NOT my normal stuff. There won't be a lot of fluff or comfort. It's a lot of pain and suffering, so please heed the tags and read at your own risk. 
> 
> NOTE: Because I'm a masochist, I decided to also do Kinktober this year as well. So, if you like the fluffy, kinky side of my fics, go check that one out instead :)

**Summary for the Chapter:**

> \- Waking up restrained  
> \- Shackled   
> \- Hanging

The first thing Dean becomes aware of when he comes around is the intense pain in his arms. His shoulders are pulled at an odd angle, his wrists restrained high above his head. He gingerly wiggles the toes that should be in his left boot but are chillingly bare and finds only air. 

Slight panic settling into his chest, he stretches his toes until they brush against cold concrete. He shivers involuntarily and hisses when it pulls his overextended shoulders. He centers himself as best he can, but when he opens his eyes, all he sees is black. 

There’s a dark chuckle from somewhere to his right, a loud growling so close to his left ear he scrambles to get away from it. However, with his hands restrained and unable to properly grip the floor it only sets him about swaying… into a set of sharp claws that easily slice into his chest. 


	2. Collars/ Kidnapped/ "Pick Who Dies"

**Summary for the Chapter:**

> \- "Pick who dies"

**Notes for the Chapter:**

> The italics indicate its a nightmare.

_ It only takes a second for the horde of demons to overwhelm them. Mom and Dean on opposite sides of the stage while Crowley stands in the middle, snarling at him. “Go ahead Moose, make your choice!” He vanishes only to reappear at Sam’s side.  _

_ He grabs a fistful of Sam’s hair and jerks his head up painfully so he can see the impossible choice before him.  _

_ “Choose now or I kill both of them,” Crowley whispers, licking the shell of his ear. Sam cringes.  _

_ His eyes flicker between his brother and Mary.  _

_ He’s just starting to get to know her, learn what’s she’s really like. He’s wanted her in his life for so long, but…  _

_ Tears stream down his face before he lifts his eyes to his mother. She smiles kindly though her eyes tear up. She nods, accepting his decision.  _

_ “Kill her!”  _

_ Sam holds her gaze as the knife slides across her throat, the last thing she sees the son who sent her to her execution.  _


	3. Manhandled/ Forced To Get On Knees/ Held at Gunpoint

**Summary for the Chapter:**

> \- Manhandled  
> \- Forced to get on knees  
> \- Held at gunpoint

“Get on your knees, bitch!” 

Dean complies though his jaw ticks angrily. He’s biding his time, waiting for the perfect moment to snatch the gun out of creep’s hands. 

A boot to his back sends him lurching forward, only the scrape of his palms on the rough concrete saving him. 

Realizing what a vulnerable position he’s suddenly in, Dean scrambles to rise back up onto his knees, but the guy is anticipating it. 

A hand clenches around his throat, cutting off his air supply while the jangle of a belt buckle sends terror rushing through Dean’s veins. 

He claws at the hand holding him tight, struggling against the weight now pressing against him.  _ No! No!  _ He would scream if he could only suck down even a strained gasp of precious oxygen. But instead, he’s helpless, trapped beneath the man’s weight as he kicks Dean’s legs apart. 

Something sharp and cold trails down his back and he shivers, not from cold, but the mind-numbing fear. He knows that feeling-- has felt it a thousand times before on his throat, his chest, even his wrists, and inner thighs. The sharp edge of the blade slips beneath the waistband of his jeans and tears pool in his eyes. 

_ Sammy, help! Please! Someone! Anyone!  _


	4. Caged/ Buried Alive/ Collapsed Building

**Summary for the Chapter:**

> \- Buried alive

Dean wakes in a dark place. It’s silent, nothing but his breath to be heard in the stillness. He tries to lift his hands, but they’re bound in place. He can’t move. His heart starts to race. 

Deep breaths, he thinks. Nice and slow. You’re okay. You’re alive and you’re okay. 

After a moment, he wiggles his fingers and toes-- breathes a sigh of relief when he finds they’re still mobile. Next, he gently lifts his head. Still okay. A little stiff but nothing a good shower can’t fix. 

It’s when he tries to raise his head to look around that he encounters a problem. 

His head smacks into something hard and he curses under his breath. “ _ Son of a-- _ ” His words falter when a cold realization strikes him. 

_ No...Please, God, No!  _

He twists his wrists until he can reach out with his fingers. Tears slide down his cheeks when he feels solid wood beside him on both sides. 

“No. No. No, please no… No, Oh God--” His breath speeds up, his chest heaving with each breath. He screams. 

“SAAAAMMMM!” 


	5. On the Run/ Failed Escape/ Rescue

**Summary for the Chapter:**

> \- On the run  
> \- Failed escape

Shitshitshit!

The growling gets louder and Sam spins wildly, searching for a place to hide. The wolves have his scent of course, but if he can stay hidden until his brother finds him…

A pained howl sends every hair standing on he scrambles to find purchase on the rough bark of the tree. 

C’mon, Sam! His inner monologue chastises as the soles of his boots- still muddy from the river- slip, and slide on the trunk. With a frustrated huff, he jogs back a few steps to get a running start. Just as he jumps and catches ahold of the thick branch, he feels something swipe at his hair. 

Hurriedly pulling himself the rest of the way up, he clings to the tree, shivering in the cold. The wolves pace at the base of it, waiting for him to grow weak and fall. 


	6. "Get It Out"/ "No More"/ "Stop, please"

**Summary for the Chapter:**

> \- "Get it out"  
> \- "No more"

Dean’s panting on the table, his face and upper torso slick with sweat as Sam and Bobby hold him down. 

When Garth probes the hole in his abdomen with the forceps, he screams and the strap of leather falls to the tabletop beside his head. 

Sam shushes him, leaning down to murmur to his brother, hoping to distract him from the task still ahead of Garth. 

While Sam had been fighting off the small army of snakes slithering between him and the Impala to try to get the iron spike, the mother had been sinking her fangs deep into Dean’s belly. So deep that when Sam finally jabbed the spike into her heart, Dean’s abdominal muscles had been on display, his skin ripped clean off in her final death throes. 

Now, they had to remove the venomous fangs. Without the mother’s nervous system sending the signal to release the venom, the only risk was if Garth pulled them out too quickly or shattered one of them while still inside Dean. 

They couldn’t sedate him, the risk of Dean falling into a coma too high, so they had no choice but to restrain him while Garth used his nimble, steady hands to remove the fangs. 

Dean’s breathing was faltering, his eyelashes fluttering as he fought to stay conscious through the ordeal. 

When his hand went limp in Sam’s, his brother’s vision went red. “GET IT OUT OF HIM, GARTH!  _ NOW! _ ” 

“I’m trying, Sam, but--” 

Sam looked up at the other hunter, his eyes steely with barely subdued violence. His voice was low but the threat was clear. “My brother is dying, Garth. And so help me God, if Dean dies, I will tear you apart.” 

Garth gulped before picking up the tongs. His hand was shaking thanks to Sam’s threat so he had to take a calming breath to ground himself before he adjusted the gauze soaking up most of the blood and renewed his efforts. 

“Dean? DEAN! C’ mon, Dean, stay with me!  _ Garth _ !” 

The tip of the tongs brushed against something hard and Garth focused on that spot. Just a little to the left…  _ There!  _

He gripped the root of the long fang and pulled hard. 

“GAHHH!” Dean’s eyes flew open and he struggled anew, white-hot pain lancing through his abdomen. 

Tears streaming down his face, he leaned to the side as he vomited. Shivering violently, he clung to his brother, Sam shushing him as he sobbed, “No more, Sammy. Please, no more...I can’t…” 

“Shhh, it’s okay, big brother, I got you. You’re okay.” 

Looking over Dean’s shoulder, Sam met Garth’s eyes and nodded.  _ One more to go _ .


	7. Support/Caring/Enemy to Caregiver

**Summary for the Chapter:**

> \- Enemy to Caregiver

**Notes for the Chapter:**

> Chanelle, sweetie, here's a little ficlet for your prompt :)

“My God, don’t tell me you actually  _ like  _ living here, Feathers. This place is a squalid dung heap!” 

“...Crowley?” Cas blinked blearily into the dim lighting. 

Sure enough, standing at the end of the couch on which he laid was The King of Hell, himself, decked out in a three-piece suit and scowling at his taste in movies, apparently. 

“Chuck Norris? The Lone Ranger? ...Spirited Away?” Crowley raised an eyebrow in the angel’s direction before tutting. “Such a shame to see you’re following in Squirrel’s footsteps when it comes to multimedia.”

Cas coughed into the threadbare blanket before asking, “What’s wrong with them?” He yawned widely, exhausted by his vessel’s betrayal. 

Instead of answering, Crowley frowned at him. “You look poorly, Feathers. What have the Winchesters gone and gotten you tangled up in now?” 

Half-asleep, Cas brushed the concerned tone off as delirium due to his fever. Crowley didn’t care for him. 

Crowley took a hesitant step towards Castiel’s sleeping form, wincing when he felt the heat radiating off of the angel’s body.  _ Former angel _ , he corrected himself. Cas was human now, which meant he was susceptible to human ailments such as fevers and nasty chest colds. 

Sitting gingerly on the edge of the couch, he gasped when Cas snuggled into him, his dripping nose smearing onto Crowley’s dress slacks. The King grimaced and rose to fetch a towel, but stopped when he saw the pathetic state of the bedroom.  _ Yeesh, even the Winchesters don’t let it get this bad… _

After a brief pause, Crowley gave a quick nod then snapped his fingers. 

One of his loyal servants appeared immediately, ready to do whatever he asked, no matter how odd. And today’s request was quite the oddball… 

“ I want this place spic n’ span by the time return. Do you understand?” His subject nodded. “Do not under  _ any _ circumstances disturb him. If you do, I will have you…” He pondered for a moment before grinning, “...drawn and quartered then put back together and fed to my hound.”

The demon gulped loudly before nodding again. “Yes, my King. No one will touch the-- him.” 

“You have one hour. Do not disappoint me.” The demon stayed standing there and Crowley rolled his eyes. "Go!" 

Once Dave?--Bob?--Fred?-- _Oh, who the hell cares what Unimportant Demon #3's name is anyway--_ left, Crowley was left in a bind of sorts. If he stayed, he might be expected to...take care of...the former angel. But if he left, Cas might consider it well, inconsiderate. 

He paced up and down the hallway, trying to decide what to do-- whether it would be a better representation of his title as Ruler of Hell to stay and care for Castiel or leave him lying on the Winchester's doorstep in a mock-up of ding-dong-ditch. 

A rattling cough came from the living room. He definitely did _not_ jump. He just...tripped over the worn spot in the carpet. 

Grumbling as he strode up to the couch, Crowley took in the sight of the once fearsome angel and almost snorted. Cas's hair was flat on one side, yet sticking straight up on the other, his nose was as red as a freshly beaten bottom, and he was shivering so hard it looked as if he would shatter any moment. 

Cas had the gall to look at him with a (poor) imitation of Moose's sad-puppy eyes. "What?" he snapped. "What do you want?" 

Cas sighed, "I don't know. I just-- Um, sometimes when Sam is sick, Dean sits with him and...I thought, maybe..." 

"You want _me_ , King of Hell, to sit with _you? "_ Okay, so maybe that was a tad much, but honestly! He had subjects and proclamations and people to murder and torture and...

_Bollocks._

Crowley sat down on the couch with a huff. "Fine. But if you _ever_ tell anyone about this, I will string you up by your toes and cover you in nutella." 

Cas frowned. "And that would be a punishment?" 

"Yes, Feathers. Because after I string you up and cover your entire vessel, naughty bits included, with chocolatey-hazelnut goodness, I would leave you alone in a room with Juliet." He turned to give Cas a smarmy smile. "You do remember my hound, don't you, Cas?" 

Cas gulped. 

Crowley chuckled and stuck his hand out. "So, do we have a deal, then?" 

Cas nodded. "Deal." 


	8. "Don't Say Goodbye"/ Abandoned/ Isolation

**Summary for the Chapter:**

> \- "Don't say goodbye"   
> \- Abandoned  
> \- Isolation

“No! Please, Robby, you said we were in this together! You can’t leave now!” 

Dean heard the kid’s frantic run to the door. 

“ROBBY!” 

Impossibly, he felt a small sliver of empathy toward his captor. 

It was obvious from the dynamic he’d witnessed in the last six hours stuck in this run-down shack in the middle of Bumfuck, Nowhere, that the boy, Christian, and Robby were brothers. 

Robby had been waiting for Christian to return with Lyla, the young werewolf Sam and Dean had saved. But when the older man had seen Dean as well, he’d flipped his lid. 

_ “What the hell, Chris!? I told you no witnesses and no extras! Who the fuck is that?!”  _

They obviously had made any contingency plans but when Christian barged into Lyla’s apartment and found her and Dean making out on the couch, he’d had to improvise. The kid was smart, Dean had to admit... he’d grabbed the pepper shaker off of the kitchen table and tossed it at the hunter so he could grab Lyla. Dean’s eyes had watered so bad he couldn’t see shit, so he’d pulled Lyla behind him while he choked and sneezed. 

Christian had tackled him and knocked him out, but after apparently determining Dean was a hunter, taken them both. 

Now, Sam was on his way and Christian was on his own. 

Smothering his brotherly sympathies, Dean smiled at the young girl asleep on his shoulder.  _ Well, well, Big Bad Wolf...Who’s the Little Pig, now? _


	9. "Take Me Instead"/ "Run!"/ Ritual Sacrifice

**Summary for the Chapter:**

> \- Ritual sacrifice

As soon as they shoved him through the door, Dean’s blood ran cold. 

It was a strange cathedral-like cavern, with ancient-looking torches lining the way to the middle of it. And there, on a large stone dais, surrounded by twelve women in blood-red robes was Sam. 

“SAM!” He cried, struggling against the freakishly strong women dragging him to the chains on the walls. So he could watch as they sacrificed his brother. “SAMMY!” 

The red-haired one lifted a long wooden stick and smacked him in the chest. 

“Son of a bit--” Before he could finish speaking, the second one punched him in the jaw. Blood dripping from his busted lip, Dean’s head hung, but his eyes never strayed from the prone figure in the center of the room. 

“Why are you doing this?” he asked, panting from exertion. He flinched when they closed the shackles around his wrists. 

“We have waited long for our Master to return. It is time for him to be reborn in the vessel of perfection..”

“Your Master?” 

The women spoke in unison, bowing low. “Adonis, the great and beautiful.” 

Dean blinked. “What.” 

Part of him wanted to laugh, but the other, stronger part wanted to rip their friggin’ heads off. How dare they try to shove a God all up in Sammy! First, he’d had to deal with being the vessel of Lucifer, and now, these crazy bitches wanted to shack him up with some narcissist who got done in by a fucking pig?! Oh, hell no! 

“Listen, _sister_ , you can take your Adonis-worshipping bitch bunch and go find someone else because you lay _one_ _finger_ on my brother and I will kill you all!” 

Dean searched the area around him for any way to escape the chains, but the walls were solid rock that refused to crumble and they’d moved everything out of his limited reach. 

Sam, however, had been left untethered… 

“SAMMY! WAKE UP!” Dean banged his fists against the stone, rattling his chains as loudly as he could. “GET UP! SAM!” There was no response from his brother. 

Dean licked his bloodied lip-- Desperate times call for desperate measures… 

“Sam, If you don’t get your ass up  _ right now _ , I swear to God I will fling your precious laptop out of the window the next time I’m doing sixty!” 

Sam’s eyes flew open. 


	10. Blood Loss/ Internal Bleeding/ Trail of Blood

**Summary for the Chapter:**

> \- Blood loss  
> \- Trail of blood

_ Sam pushed the door open and stepped inside. It was empty save for the trail of crimson that led up the stairs.  _

_ Tightening the grip on his Beretta, he slowly climbed up to the second story.  _

_ Unlike the first floor, everything here was white. So white it was almost blinding as Sam crept along the marble floors. His eyes searched each room he passed but they were all empty.  _

_ At the end of the long hallway, the trail led him to a set of ornate doors, gilded with gold. Shaking, he pushed the door open.  _

_ His focus immediately fell to the floor. A sea of red covered it. The walls dripped with it, too, as he slipped and stumbled towards the clawfoot tub in the middle of the room. _

_ It wasn’t empty.  _


	11. Defiance/ Struggling/ Crying

**Summary for the Chapter:**

> \- Defiance  
> \- Crying

“No!” Sam shouted, stomping his little foot down on the faded carpet. 

John sighed. It couldn’t ever be easy with his youngest… 

“Sammy, I know you want to go, but you can’t. I have to go to work and Dean needs to rest.” 

“I wanna  _ go _ to the  _ park!”  _

“Sammy, I said no--” 

“But you said  _ yes yesterday! _ ” Sam argued, crossing his skinny arms over his tiny chest. 

The scowl on his little four-year-old face should be adorable, but John was exhausted after caring for a sick eight-year-old all night. Pushing aside the map of the surrounding woods where six girls had been brutally slaughtered, he raised his eyes. 

“Listen here, son-- I know you would like to go and that I said we could go today yesterday, but your brother wasn’t sick yesterday. Now, if you don’t sit down at the table and eat your Cheerios, you won’t be going to the park at all. Do I make myself clear?” 

Sam gave a disgusted huff before grudgingly stomping back over to the flimsy kitchen table. He grumbled angrily to himself as he stuck the spoon in the bowl to scoop up a bite of now-soggy cereal. 

_ “Dean would have let me go…”  _

“Sam-- enough,” John said sternly. He didn’t remember Dean being this much of a handful when he was four, but Sam...oh boy could his youngest get under his skin... 

“Sit there quietly and eat your breakfast.” 

_ “Dean lets me talk…”  _ Sam muttered, banging his heels against the rung of the chair. 

Reaching his breaking point, John snapped.  _ “I don’t care what Dean lets you do! I am your father and I am telling you to sit down, be quiet, and eat your breakfast!”  _

Sam’s eyes widened fearfully and he whimpered before shoving his chair back and running out of the room. It wasn’t hard to guess where he was going. 

Sure enough, when John followed his path down the hallway a few moments later, he wasn’t surprised to hear a tired, raspy voice attempting to calm scared, little boy sniffles. 

_ “Aw, Sammy, it’s okay. I’m sure Dad didn’t mean to yell. He’s just a little tired is all. You know? Cause he was with me most of the night.”  _

_ “C-can I stay with you…?”  _

_ “Dad won’t be happy if you get sick too, Sammy…”  _

_ “I don’t care! I don’t wanna go back out there!”  _

_ “Sammy--” _

_ “Please, Dean?”  _

_ “... alright. Come on.”  _


End file.
